US4234588A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrimidine compounds
Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1979-02-07
•
Granted: 1980-11-18
•
Expires: 1999-02-07
Abstract
Abstract The compounds are substituted pyrimidine compounds which are histamine H 2 -antagonists. A specific compound of the present invention is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Inventors
- 👤 Thomas H. Brown
- 👤 Robert J. Ife
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:33
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; A; A61; A61P; A61P1/00; A61P1/04; A61P1/14; A61P29/00; A61P43/00; A61P9/00; A61P9/12; C07D213/54; C07D213/55; C07D213/60; C07D213/61; C07D213/62; C07D213/63; C07D213/64; C07D213/78; C07D213/84; C07D213/85; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/56; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/18; C07D333/20; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
161 words
A compound of the formula: ##STR7## in which D is hydrogen or R 1 R 2 N(CH 2 ) m --, R 1 and R 2 are hydrogen, lower alkyl, phenyl(lower alkyl) or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group, m is from 1 to 6, X is oxygen or sulphur, Y is sulphur, oxygen or methylene, n is 2 or 3, Z is hydrogen or lower alkyl, A is C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and p and q are such that their sum is from 1 to 4, and B is a heteroaryl group selected from pyridyl, pyridyl N-oxide and 1,3-dioxolopyridyl optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, in the form of the free base or its pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
161 words
A compound of the formula: ##STR7## in which D is hydrogen or R 1 R 2 N(CH 2 ) m --, R 1 and R 2 are hydrogen, lower alkyl, phenyl(lower alkyl) or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group, m is from 1 to 6, X is oxygen or sulphur, Y is sulphur, oxygen or methylene, n is 2 or 3, Z is hydrogen or lower alkyl, A is C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and p and q are such that their sum is from 1 to 4, and B is a heteroaryl group selected from pyridyl, pyridyl N-oxide and 1,3-dioxolopyridyl optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, in the form of the free base or its pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
38 words
A compound of claim 1 in which R 1 and R 2 are hydrogen, lower alkyl or 2-phenylethyl or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group.
Claim 4
Dependent Claim
15 words
A compound of claim 2 in which R 1 and R 2 are both methyl.
Claim 5
Dependent Claim
15 words
A compound of claims 1, 2 or 3 in which m is 1 to 3.
Claim 6
Dependent Claim
10 words
A compound of claim 1 in which D is hydrogen.
Claim 7
Dependent Claim
10 words
A compound of claim 1 in which X is oxygen.
Claim 8
Dependent Claim
12 words
A compound of claim 1 in which Y is sulphur or methylene.
Claim 9
Dependent Claim
10 words
A compound of claim 1 in which Y is sulphur.
Claim 10
Dependent Claim
10 words
A compound of claim 1 in which n is 2.
Claim 11
Dependent Claim
10 words
A compound of claim 1 in which Z is methyl.
Claim 12
Dependent Claim
10 words
A compound of claim 1 in which Z is hydrogen.
Claim 13
Dependent Claim
11 words
A compound of claim 1 in which A is α,ω-straight alkylene.
Claim 14
Dependent Claim
10 words
A compound of claim 12 in which A is methylene.
Claim 15
Dependent Claim
29 words
A compound of claim 1 in which A is --(CH 2 ) p W(CH 2 ) q -- where p is 0, W is oxygen and q is 1.
Claim 16
Dependent Claim
37 words
A compound of claim 1 in which B is a 2-pyridyl, 3-pyridyl or 4-pyridyl group, which group is optionally substituted by one or more lower alkyl or lower alkoxy groups, or a pyridyl group substituted by hydroxy.
Claim 17
Dependent Claim
17 words
A compound of claim 1 in which B is 3-pyridyl, 6-methyl-3-pyridyl, 5,6-dimethyl-3-pyridyl, 6-methoxy-3-pyridyl, 2-methoxy-4-pyridyl, 6-hydroxy-3-pyridyl or 2-hydroxy-4-pyridyl.
Claim 18
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Claim 19
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
Claim 20
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone.
Claim 21
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone.
Claim 22
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyrimidone.
Claim 23
Dependent Claim
10 words
The compound of claim 15, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone pyrid-N-oxide.
Claim 24
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Claim 25
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Claim 26
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
Claim 27
Dependent Claim
9 words
The compound of claim 5, said compound being 2-[2-(2-thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Claim 28
Dependent Claim
10 words
The compound of claim 1, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone trihydrochloride.
Claim 29
Dependent Claim
10 words
The compound of claim 1, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone trihydrochloride.
Claim 30
Dependent Claim
31 words
A pharmaceutical composition having histamine H 2 -receptor blocking activity comprising in an effective amount to block said receptors a compound of claim 1 and a pharmaceutically acceptable diluent or carrier.
Claim 31
Dependent Claim
15 words
A pharmaceutical composition of claim 29, comprising 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone and a pharmaceutically acceptable diluent or carrier.
Claim 32
Dependent Claim
30 words
A method of blocking histamine H 2 -receptors which comprises administering to an animal in need thereof in an effective amount to block said receptors a compound of claim 1.
Claim 33
Dependent Claim
36 words
A method of simultaneously blocking histamine H 1 -receptors and histamine H 2 -receptors which comprises administering to an animal in need thereof in an effective amount to block said receptors a compound of claim 5.
Claim 34
Dependent Claim
19 words
A compound of claim 1, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone in the form of a pharmaceutically acceptable acid addition salt.
Claim 35
Dependent Claim
25 words
A pharmaceutical composition of claim 29 comprising 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone in the form of a pharmaceutically acceptable acid addition salt and a pharmaceutically acceptable diluent or carrier.
Claim 36
Dependent Claim
16 words
A pharmaceutical composition of claim 34 comprising 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone trihydrochloride and a pharmaceutically acceptable diluent or carrier.
Claim 37
Dependent Claim
12 words
A method of claim 31 in which the compound administered is 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
Claim 38
Dependent Claim
22 words
A method of claim 31 in which the compound administered is 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone in the form of a pharmaceutically acceptable acid addition salt.
Claim 39
Dependent Claim
13 words
A method of claim 37 in which the compound administered is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone trihydrochloride.
Claim 40
Dependent Claim
13 words
A compound of the formula: ##STR8## in which R is hydrogen or methyl.
Claim 41
Dependent Claim
13 words
A compound of the formula: ##STR8## in which R is hydrogen or methyl.
Claim 42
Dependent Claim
1 words
2-(2-Mercaptoethylamino)-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
Claim 43
Dependent Claim
1 words
2-(2-Mercaptoethylamino)-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-18 | 1984-05-19 | 1984-11-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-18 | 1988-05-19 | 1988-11-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-18 | 1992-05-19 | 1992-11-18 | $7700.00 | Window Closed / Lapsed |